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Substance Name: Netilmicin [INN:BAN]
RN: 56391-56-1
UNII: 4O5J85GJJB
InChIKey: CIDUJQMULVCIBT-MQDUPKMGSA-N

Note

  • Semisynthetic 1-N-ethyl derivative of SISOMYCIN, an aminoglycoside antibiotic with action similar to gentamicin, but less ear and kidney toxicity.

Molecular Formula

  • C21-H41-N5-O7

Molecular Weight

  • 475.5829
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Enzyme Inhibitors
  • Human Data
  • Protein Synthesis Inhibitors
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Netilmicin
  • Netilmicin [INN:BAN]

MeSH Heading

  • Netilmicin

Synonyms

  • 1-N-Aethylsisomicin
  • 1-N-Ethylsisomicin
  • BRN 5316582
  • EINECS 260-146-8
  • HSDB 3584
  • Netillin
  • Netilmicin
  • Netilmicina
  • Netilmicina [INN-Spanish]
  • Netilmicine
  • Netilmicine [INN-French]
  • Netilmicinum
  • Netilmicinum [INN-Latin]
  • Netilyn
  • Nettacin
  • NTL
  • O-(2,6-Diamino-2,3,4,6-tetradesoxy-alpha-glycero-4-hexenopyranosyl-(1-4)-O-(3-desoxy-4-C-methyl-3-methylamino-beta-L-arabinopyranosyl-(1-6)-2-desoxy-N1-ethyl-D-streptamin
  • UNII-4O5J85GJJB
  • Vectacin
  • Zetamicin

Systematic Names

  • D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl(1-4))-2-deoxy-N(sup 1)-ethyl-
  • D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N1-ethyl-
  • Netilmicin

Registry Numbers

CAS Registry Number

  • 56391-56-1

FDA UNII

  • 4O5J85GJJB

Related Registry Number

  • 56391-57-2 (sulfate (2:5) salt)

System Generated Number

  • 0056391561

Structure Descriptors

InChI

1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3/t11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1

InChIKey

CIDUJQMULVCIBT-MQDUPKMGSA-N

Smiles

CCN[C@@H]1C[C@H](N)[C@@H](O[C@H]2OC(=CC[C@H]2N)CN)[C@H](O)[C@H]1O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intramuscular 125mg/kg (125mg/kg) BRAIN AND COVERINGS: "CHANGES IN CIRCULATION (HEMORRHAGE, THROMBOSIS, ETC.)"

BLOOD: HEMORRHAGE

LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA
Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 816, 1981.
dog LDLo subcutaneous 500mg/kg (500mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BLOOD: HEMORRHAGE
Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 816, 1981.
guinea pig LD50 intramuscular 181mg/kg (181mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BLOOD: HEMORRHAGE
Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 816, 1981.
guinea pig LD50 subcutaneous 207mg/kg (207mg/kg) BLOOD: HEMORRHAGE

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 816, 1981.
human TDLo intravenous 52mg/kg/7D-C (52mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES Canadian Medical Association Journal. Vol. 120, Pg. 161, 1979.
mouse LD50 intravenous 40mg/kg (40mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 29, Pg. 543, 1986.
rat LD50 intravenous 25200ug/kg (25.2mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BLOOD: HEMORRHAGE
Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 816, 1981.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -2.500 (none)   EST
Water Solubility 1.00E+06 mg/L 25 EST
Vapor Pressure 1.26E-18 mm Hg 25 EST
Henry's Law Constant 7.48E-35 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.86E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.